PL213828B1 - New 2"-(2''-hydroxyizopropyl)-dihydrofurane[2'', 3'';3', 4'] -2',4-dihydroxy-6'-methoxydihydrochalcone and process for the preparation thereof - Google Patents
New 2"-(2''-hydroxyizopropyl)-dihydrofurane[2'', 3'';3', 4'] -2',4-dihydroxy-6'-methoxydihydrochalcone and process for the preparation thereofInfo
- Publication number
- PL213828B1 PL213828B1 PL396023A PL39602311A PL213828B1 PL 213828 B1 PL213828 B1 PL 213828B1 PL 396023 A PL396023 A PL 396023A PL 39602311 A PL39602311 A PL 39602311A PL 213828 B1 PL213828 B1 PL 213828B1
- Authority
- PL
- Poland
- Prior art keywords
- dihydroxy
- new
- formula
- methoxydihydrochalcone
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 241000223218 Fusarium Species 0.000 claims description 5
- 241000223221 Fusarium oxysporum Species 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 2
- YKGCBLWILMDSAV-GOSISDBHSA-N Isoxanthohumol Natural products O(C)c1c2C(=O)C[C@H](c3ccc(O)cc3)Oc2c(C/C=C(\C)/C)c(O)c1 YKGCBLWILMDSAV-GOSISDBHSA-N 0.000 claims description 2
- FUSADYLVRMROPL-UHFFFAOYSA-N demethylxanthohumol Natural products CC(C)=CCC1=C(O)C=C(O)C(C(=O)C=CC=2C=CC(O)=CC=2)=C1O FUSADYLVRMROPL-UHFFFAOYSA-N 0.000 claims description 2
- ORXQGKIUCDPEAJ-YRNVUSSQSA-N xanthohumol Chemical compound COC1=CC(O)=C(CC=C(C)C)C(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1 ORXQGKIUCDPEAJ-YRNVUSSQSA-N 0.000 claims description 2
- UVBDKJHYMQEAQV-UHFFFAOYSA-N xanthohumol Natural products OC1=C(CC=C(C)C)C(OC)=CC(OC)=C1C(=O)C=CC1=CC=C(O)C=C1 UVBDKJHYMQEAQV-UHFFFAOYSA-N 0.000 claims description 2
- 235000008209 xanthohumol Nutrition 0.000 claims description 2
- 238000013048 microbiological method Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VZYFIRZLCBVYJR-UHFFFAOYSA-N acetonitrile;dichloromethane;formic acid Chemical compound CC#N.OC=O.ClCCl VZYFIRZLCBVYJR-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Przedmiotem wynalazku jest nowy 2''-(2'”-hydroksyizopropylo)-dihydrofurano[2'',3:3',4']-2',4-dihydroksy-6'-metoksydihydrochalkonu, o wzorze 2 przedstawionym na rysunku oraz sposób jego wytwarzania.The subject of the invention is a new 2 "- (2" - hydroxyisopropyl) -dihydrofurano [2 ", 3: 3 ', 4'] - 2 ', 4-dihydroxy-6'-methoxydihydroochalcone, with the formula 2 shown in the figure and the method of its production.
Związek ten jest biologicznie czynny i może mieć zastosowanie w przemyśle spożywczym i farmaceutycznym.This compound is biologically active and can be used in the food and pharmaceutical industries.
W dostępnej literaturze nie znaleziono doniesień o przedmiotowym związku ani o sposobach jego otrzymywania.There are no reports of the compound in question or of the methods of its preparation in the available literature.
Istotą wynalazku jest nowy 2”-(2”'-hydroksyizopropylo)-dihydrofurano[2”,3”:3',4']-2',4-dihydroksy-6'-metoksydihydrochalkon, o wzorze 2.The essence of the invention is a new 2 "- (2" "- hydroxyisopropyl) -dihydrofuran [2", 3 ": 3 ', 4'] - 2 ', 4-dihydroxy-6'-methoxydihydroochalcone, of formula 2.
Istotą wynalazku jest także sposób otrzymywania tego związku, polega na tym, że substrat, którym jest ksantohumol, o wzorze 1, poddaje się biotransformacji kulturą grzyba z gatunku Fusarium avanaceum albo Fusarium oxysporum.The essence of the invention is also the method of obtaining this compound, consisting in the fact that the substrate, which is xanthohumol of the formula I, is biotransformed with a culture of a fungus of the species Fusarium avanaceum or Fusarium oxysporum.
Korzystnie jest, gdy reakcję prowadzi się wodną kulturą szczepu, przy ciągłym wstrząsaniu reagentów, w temperaturze 285-313K.Preferably, the reaction is carried out in an aqueous strain culture, with continuous agitation of the reactants, at a temperature of 285-313K.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w żywych komórkach kultur Fusarium avanaceum lub Fusarium oxysporum, następuje reakcja cyklizacji grupy prenylowej do pierścienia dihydrofuranowego oraz redukcji nienasyconego wiązania α,β olefinowego w substracie.Proceeding according to the invention, as a result of the action of the enzyme system contained in the living cells of Fusarium avanaceum or Fusarium oxysporum cultures, the cyclization of the prenyl group to the dihydrofuran ring and reduction of the α, β olefin unsaturation in the substrate takes place.
Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmów, znanym sposobem, przez ekstrakcję octanem etylu.The product obtained in this way is separated from the aqueous culture of microorganisms in a known manner by extraction with ethyl acetate.
Zasadniczą zaletą wynalazku jest otrzymanie, w łagodnych warunkach, 2”-(2”'-hydroksyizopropylo)-dihydrofurano[2”,3”:3',4']-2',4-dihydroksy-6'-metoksydihydrochalkonu, jako głównego produktu reakcji w kulturze Fusarium avanaceum z wydajnością 24,6% oraz w kulturze Fusarium oxysporum z wydajnością 10,2%.The main advantage of the invention is to obtain, under mild conditions, 2 "- (2" "- hydroxyisopropyl) -dihydrofuran [2", 3 ": 3 ', 4'] - 2 ', 4-dihydroxy-6'-methoxydihydrochalcone as the main of the reaction product in the Fusarium avanaceum culture with the efficiency of 24.6% and in the Fusarium oxysporum culture with the efficiency of 10.2%.
Wynalazek jest bliżej objaśniony w przykładach wykonania.The invention is explained in more detail in the working examples.
P r z y k ł a d 1. Do kolby o pojemności 300 cm3, w której znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku, wprowadza się grzyby Fusarium avanaceum. Po 2 dniach wzrostu drobnoustrojów w temperaturze 303K i przy ciągłym wstrząsaniu, dodaje się 30 mg ksanto3 humolu, o wzorze 1, rozpuszczonego w 1,5 cm3 acetonu. Transformację prowadzi się przy ciągłym wstrząsaniu przez 7 dób. Następnie, uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie octanem etylu, osusza siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymuje się 38,9 mg surowego produktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chlorek metylenu-acetonitryl-kwas mrówkowy w stosunku 80:10:1.EXAMPLE 1 To a flask of 300 cm 3, which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku introduced into Fusarium avanaceum. After 2 days of microbial growth at 303K and with continuous shaking, 30 mg of xanto 3 humol, formula 1, dissolved in 1.5 cm 3 of acetone, are added. The transformation is carried out under continuous shaking for 7 days. Thereafter, the resulting transformation solution was extracted three times with ethyl acetate, dried with magnesium sulfate and the solvent was evaporated. 38.9 mg of crude product are obtained, which product is purified by chromatography using 80: 10: 1 methylene chloride-acetonitrile-formic acid as eluent.
Po oczyszczeniu otrzymuje się 7,75 mg związku o wzorze 2 (wydajność 24,6%).After purification, 7.75 mg of the compound of formula 2 are obtained (24.6% yield).
P r z y k ł a d 2. Do kolby o pojemności 300 cm3, w której znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku, wprowadza się grzyby Fusarium oxysporum. Proces prowadzi się jak w przykładzie 1, z tym że, biotransformację prowadzi się przez 16 dób. Otrzymuje się 34,4 mg surowego produktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaninę chlorek metylenu-acetonitryl-kwas mrówkowy w stosunku 80:10:1.EXAMPLE 2 To a flask of 300 cm 3, which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku introduced into Fusarium oxysporum. The process is as in Example 1, except that the biotransformation is carried out for 16 days. 34.4 mg of crude product are obtained, which product is purified by chromatography using 80: 10: 1 methylene chloride-acetonitrile-formic acid as eluent.
Po oczyszczeniu otrzymuje się 3,2 mg związku o wzorze 2 (wydajność 10,2%).After purification, 3.2 mg of the compound of formula 2 are obtained (10.2% yield).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR aceton-cfe: δ [ppm] = 1,22 (3H, s, H-1”’), 1,25 (3H, s, H-3'”), 2,82-2,87 (2H, m, Η-β), 3,01 (1H, dd, J = 15,1, 9,6 Hz, H-3''a), 3,07 (2H, dd, J = 15,1, 7,9Hz, H-3''b), 3,23-3,25 (2H, m, H-α), 3,91 (3H, s, 6'-OCH3), 4,75 (1H, dd, J = 9,6, 7,9 Hz), 6,06 (1H, s, H-5'), 6,75 (2H, d, J = 8,5 Hz, H-3/5), 7,09 (2H, d, J = 8,5 Hz); 14,04 (2'-OH); 1H NMR acetone-cfe: δ [ppm] = 1.22 (3H, s, H-1 ''), 1.25 (3H, s, H-3 ''), 2.82-2.87 ( 2H, m, Η-β), 3.01 (1H, dd, J = 15.1,9.6 Hz, H-3'''a), 3.07 (2H, dd, J = 15.1, 7.9Hz, H-3''b), 3.23-3.25 (2H, m, H-α), 3.91 (3H, s, 6'-OCH3), 4.75 (1H, dd , J = 9.6, 7.9Hz), 6.06 (1H, s, H-5 '), 6.75 (2H, d, J = 8.5Hz, H-3/5), 7 0.90 (2H, d, J = 8.5Hz); 14.04 (2'-OH);
13C NMR aceton-cfe: δ [ppm] = 25,4 (C-3'”), 26,0 (C-1”), 27,3 (C-3”), 30,8 (C-β), 46,9 (C-α), 56,5 (C6'-OCH3), 71,5 (C-2'”), 86,5 (C-5'), 92,7 (C-2”), 106,3 (C-3'), 106,4 (C-1'), 116,0 (C-3/5), 130,2 (C-2/6), 133,3 (C-1), 156,5 (C-4), 162,6 (C-6'), 165,1 (C-4'), 168,2 (C-2'), 205,6 (C=O); UV (MeOH)Xmax 295,1 nm. 13 C NMR acetone-cfe: δ [ppm] = 25.4 (C-3 "), 26.0 (C-1"), 27.3 (C-3 "), 30.8 (C-β ), 46.9 (C-α), 56.5 (C6'-OCH3), 71.5 (C-2 ""), 86.5 (C-5 '), 92.7 (C-2 " ), 106.3 (C-3 '), 106.4 (C-1'), 116.0 (C-3/5), 130.2 (C-2/6), 133.3 (C- 1), 156.5 (C-4), 162.6 (C-6 '), 165.1 (C-4'), 168.2 (C-2 '), 205.6 (C = O) ; UV (MeOH) Xmax 295.1 nm.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL396023A PL213828B1 (en) | 2011-08-19 | 2011-08-19 | New 2"-(2''-hydroxyizopropyl)-dihydrofurane[2'', 3'';3', 4'] -2',4-dihydroxy-6'-methoxydihydrochalcone and process for the preparation thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL396023A PL213828B1 (en) | 2011-08-19 | 2011-08-19 | New 2"-(2''-hydroxyizopropyl)-dihydrofurane[2'', 3'';3', 4'] -2',4-dihydroxy-6'-methoxydihydrochalcone and process for the preparation thereof |
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| Publication Number | Publication Date |
|---|---|
| PL396023A1 PL396023A1 (en) | 2012-01-30 |
| PL213828B1 true PL213828B1 (en) | 2013-05-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| PL396023A PL213828B1 (en) | 2011-08-19 | 2011-08-19 | New 2"-(2''-hydroxyizopropyl)-dihydrofurane[2'', 3'';3', 4'] -2',4-dihydroxy-6'-methoxydihydrochalcone and process for the preparation thereof |
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| PL396023A1 (en) | 2012-01-30 |
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